Synthesis and biological evaluation of some N-substituted indoles

Abstract

The esterification of 1-alkyl/aryl-3-ethoxy carbonyl-5-hydroxy-2-methyl indoles (1a-g) with ethyl chloroacetate and ethyl chloroformate, afforded ethyl 5-(ethoxycarbonyl) methoxy]-1-alkyl/aryl-2-methyl-indole-3-carboxylate (2a-g) and 3-(ethoxycarbonyl)-1-alkyl/aryl-2-methyl-1H-indol-5-yl ethyl carbonate (3a-g) respectively. The reaction of 1b-g with monochloroacetic acid and 2-chloropropionic acid afforded the corresponding indole acetic acid (4b-g) and propanoic acid (5b-g) derivatives respectively. These newly synthesized compounds were evaluated in vivo for potential anti-inflammatory and analgesic activities and the results were compared with indomethacin. These analogues were administered p.o. at a dose level of 20 mg/kg.